Mobile computing technologies are extending how people can interact with educational and training content in a whole new way. Through high resolution displays, intuitive user interfacing, embedded sensing technologies, and well supported app development communities, there is a plethora of content that can be used to build effective materials that target knowledge and skill development. To truly enhance this new training paradigm, extending Intelligent Tutoring System (ITS) to support mobile interactions can provide a new means to managing training in a rich contextualized environment. In this instance, learning takes place in the natural environment where directed experiences focus on the elements surrounding one’s location. In this paper, we describe the development of a new mobile ITS application using the Generalized Intelligent Framework for Tutoring (GIFT; Sottilare, Goldberg, Brawner & Holden, 2012). The domain of land navigation was applied as a use case, with direct support for the United States Military Academy at West Point. We describe the training concept, how GIFT was extended to support this concept from an architectural and assessment standpoint, along with implementation plans for an initial training effectiveness study.